Cherundolo, now 39, has been acting as an assistant coach with the USA during the November international break, sharing the insights he picked up during an impressive 15-year playing career with the 96ers. He feels it is important that 20-year-old Pulisic, widely considered the most talented American player of his generation, continues on his upward trajectory.
"Pulisic is at a club where they play a style of soccer that suits him, he's done really well at Dortmund," Cherundolo said after Pulisic became the youngest ever player to captain the USA in the recent friendly loss to England at Wembley. "Now it's just a matter of continuing to grow, staying hungry and taking on more of a leadership role with this team."
Watch: Pulisic's top three goals for Dortmund
Pulisic burst onto the Bundesliga scene in a breakout 2016/17, and has since emerged as one of the brightest attacking talents on the continent. Even though he is barely out of his teens, he is already an example for rising stars like BVB teammates Jadon Sancho and Jacob Bruun Larsen.
"I went through the exact same things as Jadon," Pulisic recently told the Evening Standard. "Whenever he is going through a tough time he knows I have been through situations like that. I am there and I can talk to him. It’s a cool relationship we have. The sky is the limit for a guy like him. You can see how much talent and how much skill he has."
While Pulisic has had to share game time with Dortmund's other wing wonders this season, he has still managed to chalk up three goals and four assists in 12 outings. Cherundolo says he now has to keep putting in the same effort that made him one of Europe's hottest prospects – and a man with over 400 competitive appearances for Hannover and 87 for the USA certainly knows a thing or two about consistency at the highest level.
"It doesn't have to be opening his mouth in the locker room, the meal rooms and all that, but on the field with performances, and bringing what he can bring to the game," the former 96ers captain explained. "His one-on-ones, setting up goals, scoring goals, being dangerous. For him now it's just plugging away, working, playing, getting better and not being complacent."
Cherundolo also touched on the opportunities that young American players are currently being afforded in Germany, with the likes of Pulisic and Schalke's Weston McKennie having already established themselves at top clubs, and highly rated talents such as Werder Bremen's Josh Sargent hoping to be the next to make the breakthrough. He believes that playing for Bundesliga clubs teaches them lessons they cannot learn on the other side of the pond.
"The biggest difference you see for Americans is on the tactical side of the game," he said. "How they respond to certain changes that happen during the game; formations, plays, how they react to that. In Germany, players from ages 16 to 18 have top-quality games week in, week out, these junior Bundesliga matches. I feel like US players don't get enough of those games at that age, where they're pushed to their level. They have to learn or they're going to fall off."
Pulisic is an ideal case in point: thanks to his Croatian heritage, he was able to obtain a European passport and play for the Dortmund academy between 16 and 18, coming of age after making the most of what he described as the "sweet spot" in his development. And if he can successfully follow Cherundolo's advice, there is no telling just how high Pulisic can fly, whether he's donning the black and yellow of BVB or the stars and stripes of the States.